might be by using the Handheld for dictation or a BT accesory which then sends the files to the BB and then it should go via email to the transcriber.

My primary questions:
is it possible to use the BB for a convenient dictation, or because of missing buttons should I right away get an external recording device ?

If I want to use the Handheld for recording and, want text to speech conversion: For privacy reasons this must be done either on the device itself (unlikely that there is an application which can do this) or at the transcriber.